


"That Wasn't So Bad, Was it?"

by jdlc9215



Category: Teen Wolf (TV)
Genre: Anal Play, Anal Sex, Bottom Derek, Gay Sex, M/M, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2013-07-04
Updated: 2013-07-04
Packaged: 2017-12-17 15:48:29
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,003
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/869246
Author URL: https://archiveofourown.org/users/jdlc9215/pseuds/jdlc9215
Summary: <blockquote class="userstuff">
              <p>Stiles loves Derek, but Derek is too big and a boy can only go so far. So Stiles wants to top. And here's the result.</p>
            </blockquote>





	"That Wasn't So Bad, Was it?"

**Author's Note:**

> Written for the 30 Day OTP Porn Challenge, info about that here: http://chasingriversong.tumblr.com/post/39525363882/30-day-otp-porn-challenge
> 
> So once I realized I didn't have to start on day two, I decided to do the prompt for the first day which was anal sex. So here is what I wrote. Again, I just finished and haven't editted at all, so if there's something that doesn't make sense, you can find a link where to message me at the bottom.

“Derek, I promise you, this is going to be fine.” Stiles said, as he held the small box carrying the black butt plug and walked to the pixie blonde cashier who had helped them select it. They had come to San Francisco for a getaway from everything; alpha packs (which was gone for good, Aiden and Ethan having joined their pack), kanimas, and most of all, good ol’ Uncle Peter, who no one likes still even after all he helped with the Alphas.   
Stiles had heard of Good Vibrations from the internet and word of the mouth. How it was the best sex store; how classy it was and how it was sex-positive. Stiles and Derek were no strangers to sex, Stiles having lost his virginity (and gotten himself a new boyfriend) when they killed Deucalion’s crazy ass. The night was filled of sexual tension built up for two years finally being broken, and words that Stiles would never hear from Derek’s mouth were spoken.   
Because Derek is Alpha, there was no way that he was bottoming. Stiles was more than willing to bottom, but when Derek’s beautiful eight inch cock was exposed, and jammed into Stiles’ hole, it took everything in him not to cry and scream as Derek pushed himself deeper and deeper into him. Stiles had said Stop, but then that turned into Don’t stop and the blood isn’t flowing into your brain when you’re having sex, it’s going into different areas.   
And Stiles’ precious hole can only be fucked so many times before he ultimately gives out, he mentioned the fact of maybe Derek bottoming. “Yeah, that’s not going to happen.” It took a lot of convincing before that not going to happen turned into a “I’ll think about it.” And that was the best response that Stiles was gonna get. At that moment.  
When Derek (of all people) mentioned to Stiles about possibly going to San Francisco for a getaway, Stiles was more than happy to say yes. They were planning to stay for a long weekend and Stiles had already compiled a list of what to see. He rarely goes anywhere outside of Beacon Hills and he was going to take full advantage of this opportunity; walking on the Golden Gate Bridge, watching the sea lions (sea dogs to him) at Pier 39, ride the BART (San Francisco version of metro trains) to an Oakland A’s game, and go to The Castro, the Nation’s best known gay neighborhood.  
In his research of the Bay Area, Stiles had come across the Good Vibrations website. And once he basically dissect that website from head to toe, he found out exactly what he needed, (among other things but that riding crop and flogger would have to wait until both him and Derek were willing to try) a butt plug. Stiles had already planted the side of Derek bottoming in his head, now he just needed to feed it. And maybe going to Good Vibrations would help out.  
When they entered the store, whose windows were covered with a white sheet to cover what was in the store, they were greeted enthusiastically. Or at least Stiles was, the blonde stepped away from Derek and Stiles was pretty sure it was because his boyfriend had made a face saying, Stay away from me.   
The blonde looked to Stiles with a smile and said, “Can I ask to see your ID?”  
The store doesn’t let in anyone who isn’t 18 look inside the store and he had a few pros and cons as to why. “Yeah, sure.”   
Once Stiles gave her the card, she looked at his birthday before making a face. Or great, here we go again. “That’s an interesting name. Gen-Geni-Geff-”  
“Stiles is fine too,” he said before she could even say that dreaded name.   
“Alright,” the short pixie blonde chuckled as she handed him back his ID. “Well I’m Kris, if you guys need him with anything and have questions about how stuff works, please let me know.” She walked back to the cash register and did whatever it was people who work at sex stores do.   
Finally after looking around the store, and putting a few vibrators in Derek’s face, which earned him a few I’m going to kill you faces, he had found the butt plug that he wanted. It was short, made exactly for beginners (meaning Derek) and it was black. He had always known that black was the color because something about the color brings out a feel of dominance. And since Derek dominates him, he figured that this suited them perfectly.  
“See, this is what is going to go inside of you, Der,” he said as he handed the butt plug to his boyfriend. Stiles could just tell that Derek wanted to kill him, and if the roles were reversed, he would have wanted to do the same. He can only imagine having your eighteen year old boyfriend saying that he wants to top you, and to prepare you for that, he brings you to a sex store to buy a butt plug that would help you out. Yeah, he would have killed himself.   
“Let’s get the damn thing and go,” Derek said, quietly but yet, still demanding. His hands had never left the pockets of his black jeans and he could tell that Derek was going to explode in any minute. As if he didn’t know that information from putting those vibrators in his face. Stiles didn’t even ask him if he wanted to feel it, and just quickly rushed to Kris so he could pay.   
“Derek, I promise you, this is going to be fine,” Stiles muttered words of encouragement before he reached Kris.   
“Will this be it?” Kris asked him kindly.  
“I think so,” Stiles said, wanting to get out and calm down his boyfriend.  
“You guys do have lube right?” Kris asked. And that made Stiles look up from his wallet. Nope, they didn’t have lube. How could he have been such an idiot and forget the lube? He was always the one who supplied it, him having a bottle of lube on hand and always having one in his room back home. Derek was always the one who initiated the act and Stiles was always prepared, so he doubted that Derek had a bottle with him.  
“Guess it wouldn’t hurt to take some.” he said with a nervous smile in his face.  
Kris walked out of the cashier register, went to where the lubes were located and walked back. “This is water based lube, the best for that silicone toy. Just put a little on it, and you’ll be ready to go.” Once Stiles handed her the cash necessary to pay, she packed the butt plug and lube in a small brown paper bag and handed it to Stiles. “Enjoy, Stiles.”  
“Thanks.” Stiles gave her the best smile he could muster up, looked to where Derek was standing at the side, only to see that he was holding the door open for him, ready to leave a long time ago. Stiles looked at Derek as he exited the store and gave him one of his best eye roll. He was already planning just how he could pay Derek back with the butt plug.

Stiles hadn’t spoken a word to Derek on their way back to the hotel in Derek’s black camaro. He just looked out the window, probably wishing he was at one of the tourist spots that he had planned for him and Derek to see. Probably wishing he was anywhere but near the vicinity of his boyfriend.  
Derek knew that he acted like a jerk back at Good Vibrations. Like a jerk and someone who was especially horny for being at a sex store. But he really didn’t want Stiles to top him. It’s not that he doesn’t trust Stiles; he loves the kid. He wouldn’t be wasting Stiles’ time if he wasn’t in love with him. He still thinks about if he could have gone a different way in proving it, but he loves him nonetheless. And it’s not the fact that he’s finally getting sex for the first time since Kate. He really loves Stiles.  
He loves the way he Stiles is even when he hasn’t taken his adderall. He loves every mole that covers Stiles’ face and body, and how he become flushed whenever something awkward happens. He (secretly) loves the way how Stiles can go on and on about one of his favorite TV shows for hours, and how he can make you feel for the characters in the show. And he loves how when he wakes up, on those days that he stays the nights and senses Stiles awake, just looking at him. He could almost hear Stiles asking himself if any of this was real. That he had finally gotten Derek after wanting him for so long. Point blank, he loves Stiles.  
But he’s not ready for Stiles to top him during sex. He just can’t give himself like that again. He doesn’t even want to think about Kate. He wishes that Kate didn’t fuck him up the way that she did. He wishes that Kate never existed. But if any of those things never happened, would they lead him to Stiles? Would they lead him to the 147 pound boy with pale skin, fragile bones and beautiful moles that covered his face?   
Stiles loves him. He has to, to even put up with all the shit that he’s gone through with Derek and still be there for him. But if he really loves him? Why hasn’t he said a single word to him? Why hasn’t he said anything since they’ve got to the hotel room? Derek couldn’t take the silence anymore.   
“Stiles,” he says as he looks up from the floor as he sits at the foot of the bed, and looks at the younger boy, sitting at the table with his phone in his hands. He looks at Derek for a second before he lays his phone on the round wooden table. “Say something.”  
Derek has his attention. Stiles gives him a worried expression before turns the chair he’s sitting in around to look at him. “What do you want to me, Der?”  
“Anything. That you’re mad, that you’re pissed off at me. Something.” Derek looks up at Stiles with those green eyes of his and it’s like they’re pleading to him. “You know I can’t take being in the same room as you and you not saying anything.”  
“Wait, you think I’m mad at you?” Stiles is up from the chair and walks over to Derek.  
“You’re acting like it,” Derek says quietly.  
“Der, you seriously can’t-” Stiles cut himself and kneeled in front of his boyfriend. “You think I’m mad at you? I’m mad at myself. I’m clearly pushing something that you’re not ready for, and for some reason, which I’m choosing to respect because you’ll open up to me about it eventually, you’re not comfortable with it yet. You’re not ready for it now, and I get that. I can bottom as much as you want me to, but I’m gonna start asking that we don’t do it a lot because Derek, I love you, but sometimes you gotta give a guy a break here. I need my rest. I need-”  
Stiles is cut off again, but only this time by Derek putting his mouth on his. The kiss comes as a surprise especially because Stiles wasn’t looking at Derek, so his eyes opened wide before he realized what was going on and kissed Derek back. Derek’s tongue licked Stiles’ lips and they parted, letting Derek’s tongue wrestle his for the dominance that Derek so clearly needs. Stiles’ moans quietly into Derek’s mouth, as Derek grabs Stiles from the floor and sits him down on his lap. They continue making out and soon, Derek is laying Stiles down on the bed.   
“Okay wait,” Stiles says breaking the kiss and trying to full his lungs with arm. “You literally take my breath away.” Stiles lays his head down on the pillow and looks back at Derek. “I’m sorry if I made you uncomfortable back there. I didn’t mean it. I’m just... Derek, I’m really sorry.”  
“No. You don’t have to apologize for anything. I should be the one that’s sorry. I acted like a spoiled brat. You were just trying to explain something you wanted to try out and it’s my fault. I keep shutting you down instead of refusing to actually listen to you. I’m sorry, Stiles.”  
Stiles shakes his head as he stares at his boyfriend, his Sourwolf. “You know no matter what you say, I’ll forgive you. I forgive you because I love you, Derek. Fucking hell, I love you.” Stiles reaches to kiss Derek again, but Derek stop him. “Okay, what’s wrong?”  
If Stiles only knew the effect that those words had on him. If he only knew what he could do with those words. It seems like all that Stiles has to say is those three words and Derek would believe that everything would be okay. Which is why he wants Stiles to get what he wants. “Baby, you can do what you want.”  
Stiles opens his eyes wide, not really sure that he heard that right. “Wait, what?”  
“You can top me baby. I love you, and I trust you.”  
Stiles is left speechless, so speechless that he lets out a chuckle because this is actually happening. This is really happening. “Oh my God, I love you so much Derek.” And that was all the warning that Stiles needed to jump and attack Derek. Soon, Derek is the one who’s laying down on the bed as Stiles takes off his shirt to reveal those amazing light brown abs of his, and starts to kiss them.  
He lays a hand on Derek’s chest, feeling his heartbeat racing through his skin. Once he gets to Derek’s belly button, he starts to lick and suck on it, some of his treasure trail hairs caress his face. Something about licking his belly button makes Stiles a wild animal and he starts to devour. Wanting to savor everything that he can. Derek starts to moan and Stiles loves knowing that this is the kind of power that he has on his boyfriend; he has Derek under his control. Only unlike so many others before him, he won’t hurt Derek. He refuses to ever hurt him.   
Stiles feels something hard press against his chest as he licks Derek’s skin. He looks down and sees the outline of Derek’s confided cock hidden in his jeans. “Look at this,” Stiles says as he grabs onto Derek’s penis through his jeans, which causes Derek to take in a quick breath of air in shock. “Look at how hard you are for me, baby.”   
“Stiles, please...” Derek starts to plead quietly.  
“I know baby. I know.” Stiles starts to unbutton Derek’s jeans to let out the one piece of Derek that can make him and yet, break him. Literally. Once the jeans are unbuttoned and unzipped, he takes off both Derek’s jeans and his black boxer briefs, releasing Derek’s beautiful penis. Unlike Derek’s smooth chest, there is hair surrounding the area around his penis and his thighs are covered with dark colored hairs.  
And there is Derek’s long hard uncut cock, looking back at Stiles, wanting to be touched. Stiles can almost hear it’s cries. He pulls back the foreskin and kisses the head, causing Derek to arch his back off the bed. He continues kissing Derek’s beautiful shaft from top to bottom, while cupping both of Derek’s balls in his hands. When he reaches his hairy balls, he doesn’t stops and takes it one step further by sucking both balls in his mouth. The slurpy sound Stiles make when he takes another ball in his mouth makes Derek buck in the bed. He can’t this torture.   
“Baby, please.”  
“I know, Der. I know. Just relax. Turn around so I can do this.” Derek listened to Stiles and turned around on his back, resting his head on a pillow. “You’re so beautiful, Derek.” If this were any other time, he would have considered giving Derek a back massage. But right now there’s something that he really wants to do. So he’ll give it to Derek some other time. He straddles himself on Derek’s thighs, grabs the butt plug and opens it from it’s box.  
He reveals the contents which is just a small booklet containing instructions, in Swedish (What, are we in Africa?), and the black silicone butt plug. Now all he needs to do is get the lube. “Come on Stiles, if you’re gonna do it, do it already.”  
Stiles comes up to Derek’s back, grabs his hands which are laid out above Derek’s hands and entwines his fingers with Derek’s. He begins kissing Derek’s back, and Derek let’s out a quiet moan. He starts kissing his left arm, biceps and his shoulder blade before he repeats the same notion with the right side.   
He trail kisses Derek and then he reaches his triskelion tattoo. Stiles says a little prayer, why, even I don’t know, and begins to kiss the tattoo. He kisses all three circles and licks the skins, before he sucks on it; almost as if the tattoo is satisfying a thirst he didn’t even know he had. Once he’s done with the tattoo, he continues kissing Derek’s back.  
When he reaches Derek’s perfect ass, he squeezes it firmly, earning him a moan from Derek, who Stiles forgot was awake for a second, considering that he hadn’t heard anything except breathes from him before. He squeezes it again, before parting both cheeks and begins licking around the hole. The skin is as smooth as the skin inside his cheeks. He repeats the notion again with the other cheek before he separates himself away from Derek.   
He looks at the plug for a second, as he holds it in his hands. Do I really wanna do this, or should I just do it myself? No, he can’t. He shouldn’t. Derek is trusting him, to prepare him for this. He can’t just stick his dick in there without... Oh fuck it, yes he can. Every indication that says he could is right there hidden beyond his jeans. Fuck it, he thinks.   
He throws the butt plug on the other side of the room, and pulls off his jeans and boxer shorts. “Stiles, what are you doing?” Derek asks lifting his head off the pillow.  
“Change of plans, baby,” Stiles says as he straddles Derek again. “It’s gonna be alright though, I promise.”   
“Stiles, no! I can’t!” Derek starts turns around, and Stiles can see the panic in his eyes. “No, I’m not doing this.”  
“Hey, hey, hey,” Stiles grabs Derek’s face and holds it in his hands. “Derek, look at me. Everything is going to be fine, I swear it’s gonna feel good. You have nothing to wrong about, please baby.” Derek tries to turn away to not look at Stiles, but he can’t do it. He, himself, is starting to want this, and he loves Stiles. And as much as what Stiles is doing isn’t what he wants, he knows that at the end of the day, Stiles loves him. And he would never hurt him.  
“Please, baby. I want this. I want it so much,” Stiles pleads. “Please,” he says one final time.  
“Alright, keep doing what you were doing.”   
“Thank you, baby. I love you so much.” Stiles resumes kissing Derek’s cheeks, sucking and licking every inch of skin. He grabs the bottle of lube he bought earlier and lubes his penis. He isn’t as big as Derek, but he knows exactly what to do and where to push Derek’s buttons. Once he finishes with his bright pink penis, he’s ready.   
“Der, get on all fours,” Stiles commands. Derek listens and gets on all fours. “Are you ready?” The younger of the two asks, ready for whatever rejection he might face from Derek.  
“Stiles, please, just do it.”   
“Alright baby, here I come. Just relax, okay.” Stiles positions himself comfortably and Derek feels something hard and heavy against his ass cheeks. And he knows that it’s Stiles’ dick. Oh shit. He tried to calm down, and listen to his breaths. One, two, three, four, fi- HOLY SHIT!!! WHAT WAS THAT!!!!  
“Stiles! Oh my God! Get out!” Derek yelled. A burning pain was spreading all over him. Like there was fire and that he was bleeding. He had to be bleeding, he just had to. “Stop! I’m begging you, stop!” Derek tried to get out, but Stiles wrapped a hand around him and kept him in place.   
“I know it hurts, Der. I know. But you have to relax okay, I’m begging you, relax.”  
“Stiles! Get out of me, or I swear I’ll rip your throat out right now!”  
“No, you won’t. You won’t because I love you, and you love me.” Stiles kept talking, but Derek wouldn’t listen, he opened his eyes and saw his calms come out of his hands. Part of him really wanted to rip Stiles apart. Stiles started kissing Derek’s shoulders and rubbing him. “Derek, I can’t do anything if you refuse to help me. If you really want me to, I’ll pull out. Just relax.”   Derek tried to breathe in and out slowly. He focused on his breathes; one, two, three. One, two, three. He must have relaxed because he went limp for a second, and Stiles must have felt that, because he was kissing Derek’s back. “Now, do you want me to pull out?”  
“No,” Derek muttered through closed teeth. “It’s starting to feel... Normal.”   
“Okay, I’m gonna start moving now” Stiles said and started to pull in and out of Derek. Derek moaned with each pull in and out as he rode Stiles. They don’t know how long exactly they had been fucking, minutes would either become fast or super slow. Stiles began kissing Derek’s back, and there were little fireworks going off in whatever part of his skin that Stiles touched. So maybe bottoming wasn’t as horrible as Derek thought.   
Stiles started to move a bit quicker and the fire that Derek felt burning him wasn’t going anywhere. It didn’t feel as bad as before but it certainly wasn’t pleasant. And apparently Stiles thought it was more than that, if judging by the noises he was making. And then Stiles hit Derek’s prostate.  
“Oh my God!” Derek yelled and he swore that Stiles could put anything in there and he would still be happy no matter what. “Please, baby, please,” Derek didn’t even know what he was begging for. But he wanted it. “Stiles, please!”  
“I gotcha, baby,” Stiles said and slammed into Derek again. He was about to nail him again, when he reached down and grabbed Derek’s down which was about to burst. Stiles buried himself again into Derek, slamming his prostate and it was enough to send him over the edge. And he came all over Stiles’ hand and his stomach.   
Derek didn’t have enough strength to hold them anymore, so when Stiles came down from his own orgasm and dropped over Derek’s back, they both fell onto the bed. Stiles laid on top of Derek for a few minutes before he found the strength to push himself away. His eyes remained closed, both of them feeling as if they smoked pot and the cloud was over their brains. Derek was so tired, he couldn’t feel his bones. He was just so tired.  
It was awhile before they both spoke again, Stiles breaking the silence. “That wasn’t so bad, was it?” Stiles waited for a response from Derek, but didn’t get one. He listened quietly and realized that Derek had fallen asleep. If the sleepy smile on his face was any indication, things weren’t bad at all.

**Author's Note:**

> So what did you think? What makes sense, what didn't? What did you like? What did you hate? Should I be in this fandom, should I be kicked out? Say what you have to say.  
> You can find me on tumblr at: jdlc9215.tumblr.com


End file.
